CROATICA CHEMICA ACTA

CCACAA, ISSN 0011-1643, e-ISSN 1334-417X

Croat. Chem. Acta 85 (4) (2012) 451–456.
http://dx.doi.org/10.5562/cca2123

Original Scientific Article

Synthesis, Structural Characterization and Hydrogen Bonding

of Mono(salicylidene)carbohydrazide†

Predrag Novak,a,* Tomislav Jednačak,a Jelena Parlov Vuković,b Klaus Zangger,c

Mirta Rubčić,a Nives Galić,a and Tomica Hrenara
a
Department of Chemistry, Faculty of Natural Sciences, University of Zagreb, Horvatovac 102a, HR-10000 Zagreb, Croatia
b
INA-Industrija nafte d.d., Refining & marketing business division, Product development department, Lovinčićeva bb,
HR-10002 Zagreb, Croatia
c
Institute of Chemistry, Organic and Bioorganic Chemistry, University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria

RECEIVED JUNE 29, 2012; REVISED OCTOBER 3, 2012; ACCEPTED OCTOBER 10, 2012

Abstract. The condensation reaction between carbohydrazide and salicylaldehyde in different solvents
gave mono(salicylidene)carbohydrazide (1). The structure of 1 in solution has been determined by using
experimental (NMR and UV spectroscopies and Mass spectrometry) and quantum chemical (DFT) meth-
ods. It has been demonstrated that 1 adopts the hydroxy-one tautomeric form which is in accordance with
previously published results for the related systems. Changes in NMR chemical shifts and calculations
have pointed towards a formation of intra- and intermolecular hydrogen bonds, the later being weaker and
easily broken at higher temperatures. These results can further be exploited for better understanding of the
role hydrogen bonds can play in bioactivity of related derivatives. (doi: 10.5562/cca2123)
Keywords: mono(salicylidene)carbohydrazide, hydrogen bonding, NMR and UV spectroscopy, mass
spectrometry, quantum chemical calculations

INTRODUCTION synthetic approach. One of the procedures relies on the

Schiff bases constitute a privileged class of organic
compounds, since they can easily be prepared by a con-
densation of appropriate primary amine and carbonyl
compounds.1 Although they have been extensively in-
vestigated for over a century, they still attract a consid-
erable attention.2,3 Schiff bases posses a number of
interesting biological properties,4 as well as a wide
range of analytical and industrial applications.5 On the
other hand, their ability to bind and stabilize different
metal ions in various oxidation states, not only enable
their use as reagents in analytical chemistry, but also
makes them exquisite compounds for the design of
coordination systems with biological activity.6
Among a variety of Schiff bases especially inter-
esting are those derived from di- or tri-amines. These
can be, by proper choice of carbonyl compounds, easily
tailored for construction of multinuclear coordination
systems.7 The parent amine largely dictates the nature of
the final imino product, usually giving equivalently
substituted bis- or tris- compounds of the same amino
group environment.8 However, in rare cases asymmetric-
ally substituted products can be synthesized by a proper
gradual reaction of the amino and carbonyl groups pro-
ducing first monosubstituted derivatives, and then grad-
ually higher substituted products.9–11
Mono(salicylidene)carbohydrazide (1), i.e. mono-
substituted derivative of carbohydrazide is closely related
to urea. Several examples of carbohydrazide mono-
substituted derivatives have been already described in the
literature, but all these reports lack detailed structural char-
acterization.12 Since such system offers wide possibilities
for the synthesis of asymmetric Schiff bases, we conducted
a detailed structural characterization in solution.
Hydrogen bonding is a crucial factor that affects
the overall structure and functionality of biologically
important molecules. It is also known that hydrogen
bonds are key interactions in molecular recognition
process and in binding of ligands to receptor. Many of
bioactive molecules and drugs exert their biological
activity via hydrophobic and/or hydrogen bonding inter-
actions with their biological targets.13,14 Hence, it is
important to get a closer insight into these interactions
in order to design molecules with improved biological
profile. Hydrogen bonds in solution are usually studied
by the use of various spectroscopic and theoretical

†
This article belongs to the Special Issue devoted to the 85th anniversary of Croatica Chemica Acta.
* Author to whom correspondence should be addressed. (E-mail: pnovak@chem.pmf.hr)
452 P. Novak et al., Synthesis, Structural Characterization and Hydrogen Bonding of Mono(salicylidene)carbohydrazide
Scheme 1. The structure of 1 and the atom numbering.
methods. Here, we employed one- and two-dimensional
NMR techniques, UV spectroscopy, MS spectrometry
and quantum chemical calculations to study structure
and hydrogen bonding in solution of 1. This compound
has several reactive groups which can participate in both
intra- and intermolecular hydrogen bonding (Scheme 1).
It can exist in several tautomeric forms as depicted in
Figure 1. Our previous studies on the related systems
revealed that different media (solvents) and temperature
may influence the nature and structure of hydrogen
bonds.15–18 Hence, these experiments were aimed to
explore the influence of solvents of different polarities
and temperature on the strength and structure of hydro-
gen bonding and tautomeric equilibria in 1.
EXPERIMENTAL
Materials
Carbohydrazide, salicylaldehyde, methanol, DMSO-d6
and DMF-d7 were purchased from commercial sources
and used without further purification.
Synthesis of mono(salicylidene)carbohydrazide
Carbohydrazide (0.20 g; 2.22 mmol) was stirred and
heated in 15 cm3 of methanol until complete dissolution.
Afterwards, salicylaldehyde (0.27 g; 2.22 mmol) was
added to a carbohydrazide solution and the reaction mix-
ture was stirred and heated for additional 2 hours. During
heating, white needle-like product started to deposit. The
product was filtered, washed with cold methanol (5 cm3)
and dried under vacuo. Yield: 0.32 g (74 %).
NMR Spectroscopy
NMR spectra were recorded on Bruker Avance 300 and
500 spectrometers from samples in 5 mm NMR tubes at
298 K. DMSO-d6 and DMF-d7 were used as solvents
and TMS as internal standard. Sample concentration
was 1.2×10–2 mol dm–3. Concentration dependent meas-
Figure 1. Tautomeric forms of 1.
Croat. Chem. Acta 85 (2012) 451.
urements were performed in the range 2×10–1 to 6×10–3
mol dm–3. Temperature dependent experiments were
conducted in the range 30 to 90 °C in DMSO-d6.
Proton spectra with spectral width of 6200 Hz and
a digital resolution of 0.09 Hz per point were measured
with 16 scans.
13
C proton decoupled, DEPT 90 and DEPT 135
spectra with spectral widths of 18030 Hz were collected
with 256 to 1024 scans. Digital resolution was 0.11 Hz
per point for 13C proton decoupled experiment and 0.55
Hz per point for DEPT experiments.
In the gCOSY experiment 2046 points in the f2
dimension and 256 increments in the f1 dimension were
used. For each increment 4 scans and the spectral width
of 3086 Hz were applied. Digital resolution was 3.03
and 24.39 Hz per point in f2 and f1 dimensions, respec-
tively. Typical spectral conditions for gHSQC and
gHMBC spectra were as follows. Spectral width was
2994 Hz in f2 and 16605 Hz in f1 dimension for both
experiments. 2K data points were applied in the time do-
mains and for each data set 256 and 128 increments were
collected for gHSQC and gHMBC spectra, respectively.
The resulting digital resolution was 2.94 Hz per point in f2
dimension and 125.1 and 250.0 Hz per point in f1 dimen-
sion in gHSQC and gHMBC spectra, respectively.
Phase-sensitive TPPI NOESY spectra were record-
ed under the following conditions: spectral width was
7003 Hz in both dimensions, 4K data points were applied
in time domain and 256 increments were collected for
each data set with linear prediction to 2K and zero filling
to 4K. 32 scans were applied for each increment. A relax-
ation delay was 1.5 s. The spectra were obtained with the
mixing time of 500 ms and processed with sine squared
function shifted by π/2 in both domains.
MS Spectrometry
The ESI mass spectrum was obtained on Agilent 6420
Triple Quadrupole Mass Spectrometer (Agilent Tech-
nologies, Palo Alto, CA, USA). Mass spectrum was
recorded in the range of m/z = 100 to m/z = 1500 in
positive ion mode. The sample was introduced in mass
spectrometer directly via Agilent 1200 HPLC system.
Capillary potential was 4 kV, and fragmentor voltage
135 V. Gas temperature was 350 °C, and gas flow rate
12 dm3/min. Tandem mass spectrometry was performed
with collision energy of 10 eV.
P. Novak et al., Synthesis, Structural Characterization and Hydrogen Bonding of Mono(salicylidene)carbohydrazide 453

Solution of 1 for acquiring MS spectra was pre- Table 1. 1H and 13C NMR chemical shifts for 1 in DMSO-d6
pared by dissolving 1 mg of solid in 0.1 cm3 of DMSO, and DMF-d7 at ambient temperature
and adding 0.9 cm3 of methanol.
δ / ppm (DMSO) δ / ppm (DMF)
Atom 1 13 13
UV Spectroscopy H C C(a) 1
H 13
C
α 8.20 140.05 151.37 8.46 -
UV-Vis spectra in the spectral range from 250 to 500
nm were acquired by means of a Varian Cary 3 spec- 1' 10.40 10.99
trometer using conventional quartz cells (10×10 mm). 2' 157.30 162.55 157.24
Stock solution of 1 was prepared by dissolving 3' 7.90 8.05
weighted solid in DMSO. The working solutions were 4' 4.12 4.32
prepared in 10.0 cm3 flask by adding stock solution, 1 120.49 125.70 120.01
appropriate amount of water and DMSO, resulting in
2 156.60 168.14 157.00
the mixed solvents of the volume ratios V(DMSO)/
V(H2O) = 9/1 to 1/9. 3 6.84 116.46 122.97 6.95 116.25
4 7.18 130.61 138.54 7.25 130.27
Quantum Chemical Calculations 5 6.81 119.62 125.73 6.90 119.22
All quantum chemical calculations were performed using 6 7.66 128.12 138.25 7.61 128.68
the Gaussian 09 program package.19 Geometry optimiza- OH 10.40 10.53
tion for ground and transition states were (a)
Calculated GIAO 13C chemical shifts (with respect to TMS)
performed at the B3LYP/6 311++G(d,p) level of the theo- at the B3LYP/6-311++G(d,p) level of theory.
ry.20,21 In order to increase numerical accuracy, verytight
optimization convergence criteria was used while two- 1 in solution two-dimensional NOESY sequence was
electron integrals and their derivatives were calculated by applied. Owing to a very low solubility of 1 in most of
using the pruned integration grid having 99590 points. For NMR solvents, the spectra were recorded only in
all optimized structures harmonic frequencies were calcu- DMSO-d6 and DMF-d7 solutions. The chemical shifts in
lated to insure that obtained geometries correspond to the two solvents are very similar and are given in Table 1.
local minimum (or maximum) on the potential energy Calculated GIAO 13C chemical shift shows a good
surface. Solvation effects were incorporated in the calcula- agreement with the experimental values confirming our
tions using the reformulation of polarizable continuum initial assignments. Systematic differences in calculated
model (PCM)22,23 known as integral equation formalism shifts emerge due to a balance between the accuracy
(IEFPCM) of Tomasi and coworkers.24–27 The standard determined by the method used and computational costs.
Gibbs energies of binding was calculated at T = 298.15 K As already mentioned, 1 might exist in several
and p = 101325 Pa by subtraction of Gibbs energies for tautomeric forms shown in Figure 1. Additionally, the
separate molecules from the Gibbs energy of complex. keto-tautomer in the benzene ring is also possible but it
Isotropic shieldings in vacuo and in solvent were calculat- was excluded on the basis of proton and carbon chemi-
ed by applying the gauge-independent atomic orbital cal shift values. The molecule can also adopt cis- or
(GIAO) and PCM GIAO28,29 methods on the previously trans-configuration around the C=N double bond. The
optimized geometries using the same basis set as that trans-isomer is stabilized by an intramolecular OH···N
above. Chemical shifts were calculated with respect to hydrogen bond. On the basis of NMR spectral analysis
tetramethylsilane (TMS). no trace of cis-isomer was found.
The presence of COSY correlation peak between
RESULTS AND DISCUSSION NH2 protons and neighboring NH3' proton and NOESY
cross peak between CHα and NH1' indicate that the
Synthesis dominant form in both solvents is tautomeric form 1a.
Signals of all OH and NH protons are significantly
The condensation reaction in methanol between carbo-
broadened indicating the presence of hydrogen bonding
hydrazide and salicylaldehyde in 1:1 molar ratio afford-
and chemical exchange. The large up-field shift of OH
ed mono(salicylidene)carbohydrazide.
over 10 ppm reflects strong OH···N intramolecular hydro-
gen bond (Figure 1).
NMR Assignments and Structure Elucidation
NMR chemical shifts of OH and NH1' protons
Proton and carbon chemical shifts were assigned by a show only very small changes with different solution
combined use of one- (1H, APT or 13C proton decou- concentrations, as previously reported for related sys-
pled) and two-dimensional NMR experiments (COSY, tems,12,14 corroborating that intramolecular hydrogen
HSQC and HMBC). In order to assess conformation of bonds dominate here.

Croat. Chem. Acta 85 (2012) 451.

454 P. Novak et al., Synthesis, Structural Characterization and Hydrogen Bonding of Mono(salicylidene)carbohydrazide
Figure 2. 1H NMR spectra of 1 in DMSO-d6 at (a) 30 °C, (b)
50 °C, (c) 70 °C and (d) 90 °C.
On the other hand, raising the temperature up to
90 °C in DMSO had the largest effect on NH3' protons
(0.336 ppm) and smaller effect on OH and NH1' (0.123
ppm). Both effects are shielding e.g. shifts to lower ppm
values were observed at higher temperatures (Figure 2).
The larger shift of NH3' proton is in accordance with the
fact that this group form weaker intermolecular hydro-
gen bonds with solvent molecules which are more easily
broken at higher temperatures.
Hence NMR data showed that 1 primarily exists as
hydroxy-one tautomeric form 1a in solution which is
stabilized by a strong intramolecular OH···N hydrogen
bond. Intermolecular interactions with solvent are also
present being in accordance with previously published
results.15–17
MS and UV Analysis
In MS spectrum of 1 (C8H10N4O2, exact mass is 194.08)
the base signal at m/z = 195.1 was assigned to protonat-
ed molecular ion, [M + H]+. The signal of sodium ad-
duct, [M + Na]+ appeared at m/z = 217.1, while signals
of fragment ions were at lower m/z values (120.1; 122.2;
Figure 3. MS/MS spectrum of 1 (m/z = 195.1) at 10 eV.
Croat. Chem. Acta 85 (2012) 451.
Scheme 2. Proposed fragmentation pathway of protonated
molecular ion [1+H]+ (m/z = 195.1) at 10 eV.
137.2 and 163.1). The MS/MS spectrum of 1 is shown in
Figure 3, and the proposed fragmentation in Scheme 2.
The UV-Vis spectra of 1 in DMSO and DMF are
shown in Table 2. The band at ≈ 323 nm, which was
also observed in the UV spectra of salicylaldehyde,
corresponds to the aldehide part of hydrazone. The band
at 290 nm (288 nm in DMF) can be assigned to
azomethine C=N bond,30,31 while the band in the spec-
tral region 281−283 nm can be attributed to the
hydrazide part of molecule since the broad band with
maximum at 277 nm (ε = 216.5 dm3 mol–1 cm–1) was
observed in DMSO solution of carbohydrazide.
The absorption electronic spectra of 1 were also
acquired in the mixtures of DMSO and water. The addi-
tion of water into the system caused a decrease in ab-
sorbance at higher, and increase in absorbance at lower
wavelengths (Figure 4). At the same time, a
hypsochromic shift from 323 nm to 314 nm and from
283 nm to 278 nm occur, indicating a possible E/Z
isomerisation of monosubstituted hydrazone.32,33 The
appearance of a new band in the spectral region around
400 nm, characteristic for ketoamine-enolimine
tautomeric interconversion,34,35 was not observed. This
is in accordance with NMR data.
Quantum Chemical Calculations
Optimized structures 1a–1c are presented in Figure 5
and relative standard Gibbs energies are given in Table 3.
As already indicated by NMR, the most stable
form of 1 in vacuo and in solution is hydroxy-one
Table 2. UV-Vis absorption spectra of 1.
Solvent λ / nm (10–4 ε / dm3 mol–1 cm–1)
323 (1.2996)
DMSO 290 (1.3389)
283 (1.3682)
320 (1.2553)
DMF 288 (1.5565)
281 (1.5986)
P. Novak et al., Synthesis, Structural Characterization and Hydrogen Bonding of Mono(salicylidene)carbohydrazide
Figure 4. UV-Vis spectra of 1 in DMSO and DMSO/H2O
mixtures: V(DMSO)/V(H2O)¸= 9/1, 8/2, 7/3, 6/4, 5/5, 4/6, 3/7,
2/8, and 1/9. c(1) = 1×10–4 mol dm–3. Arrows show the change
in absorbance with the increase in water content in
DMSO/H2O mixtures.
form.15 Relative differences in Gibbs energy for 1b and
1c forms in vacuo are 36.45 and 62.25 kJ mol–1 respec-
tively, while calculations incorporating the solvent ef-
fects of DMSO within the IEFPCM model gave the
differences of 56.56 and 76.31 kJ mol–1, respectively.
These values confirmed that the most dominant form in
solution is 1a.
Figure 5. Optimized structures of 1a–1c (B3LYP/6
311++g(d,p) level of the theory, solvent effects of DMSO
were incorporated using the IEFPCM method, barrier for
rotation of hydroxyl group in 1a is given).
455
Table 3. Calculated standard Gibbs energies at 298.15 K and
101325 Pa for 1a–1c (relative to 1a, B3LYP/6 311++g(d,p)
level of the theory, solvent effects were incorporated using the
IEFPCM method)
ΔrG° / kJ mol–1
Molecule
in vacuo DMSO (εr = 46.826)
1a 0.00 0.00
1b 36.45 56.56
1c 62.25 76.31
Figure 6. Optimized structures of complex between 1a with
one molecule of DMSO (B3LYP/6 311++g(d,p) level of the
theory, solvent effects of DMSO were incorporated using the
IEFPCM method).
Strength of the intramolecular hydrogen bond in
1a is 42.62 kJ mol–1 calculated in vacuo and 28.99 kJ
mol–1 in DMSO and can be categorized as moderate.36
Standard Gibbs energy of activation for the rotation of
hydroxyl group is almost twice as much as this value
(Figure 5). On the other hand, the strength of the three-
center hydrogen bond formed between NH groups and a
DMSO molecule (Figure 6) is calculated to be 11.21 kJ
mol–1 in vacuo. This supports our experimental findings
based on NMR measurements that the intermolecular
hydrogen bonds with solvent molecules are much weak-
er than the intramolecular one and are easier to break at
higher temperature.
CONCLUSION
It has been demonstrated that the mono(salicylidene)-
carbohydrazide (1) can be prepared in various solvents
by the condensation of carbohydrazide and
salicylaldehyde in different yields. The structure of 1 in
solution has been characterized by both intra- and in-
termolecular hydrogen bonding and the molecule has
been found to exist in the localized hydroxy-one
tautomeric form. Apart form intramolecular hydrogen
bonds experimental evidence and DFT calculations have
pointed towards the formation of three-center hydrogen
bonds with solvent molecules. Quantum chemical calcu-
Croat. Chem. Acta 85 (2012) 451.
456 P. Novak et al., Synthesis, Structural Characterization and Hydrogen Bonding of Mono(salicylidene)carbohydrazide
lations supported experimental findings based on NMR
measurements that the intermolecular hydrogen bonds
with solvent molecules are much weaker than the
intramolecular ones and hence easier to break at higher
temperature.
Acknowledgements. We thank the Ministry of Science, Educa-
tion and Sports of the Republic of Croatia (Project No. 119-
1191342-1083 and 119-1191342-1082) for the financial sup-
port.
REFERENCES
1. S. Patai, Carbon-nitrogen double bonds, Interscience Publishers,
John Wiley and Sons, London, 1970.
2. T. T. Tidwell, Angew. Chem. Int. Ed. 47 (2008) 1016–1020.
3. A. Blagus, D. Cinčić, T. Friščić, B. Kaitner, and V. Stilinović,
Maced. J. Chem. Chem. Eng. 29 (2) (2010) 117–138.
4. C. M. da Silva, D. L. da Silva, L. V. Modolo, R. B. Alves, M. A.
de Resende, C. V.B. Martins, and A. De Fatima, J. Adv. Res. 2
(2011) 1–8.
5. D. N. Dhar and C. L. Taploo, J. Sci. Ind. Res. 41 (1982) (8):501–506.
6. R. N. Patel, Inorg. Chim. Acta 363 (2010) 3838–3846.
7. W. X. Feng, Y. N. Hui, G. X. Shi, D. Zhou, X. Q. Lü, J. R. Song,
D. D. Fan, W. K. Wong, and R. A. Jones, Inorg. Chem.
Commun. 20 (2012) 33–36.
8. M. Cindrić, T. Kajfež Novak, and K. Užarević, J. Mol. Struct.
750 (2005) 135–141.
9. S. F. Tan and K. P. Ang, Trans. Met. Chem. 13 (1988), 64–68.
10. A. S. Munde, V. A. Shelke, S. M. Jadhav, A. S. Kirdant, S. R.
Vaidya, S. G. Shankarwar, and T. K. Chondhekar, Adv. Appl.
Sci. Res. 3 (2012) 175–182.
11. K. Užarević, M. Rubčić, V. Stilinović, B. Kaitner, and M.
Cindrić, J. Mol. Struct. 984 (2010) 232–239.
12. S. Chandra and A.K. Sharma, Spectrochim. Acta Part A 72
(2009) 851–857.
13. P. Novak and T. Jednačak, NMR spectroscopy for studying In-
teractions of bioactive molecules, in: Z Mandić (Ed.), Physico
Chemical Methods in Drug Discovery and Development, IAPC
Publishing, Zagreb, 2012. pp. 189–231.
14. P. Novak, J. Barber, A. Čikoš, B. Arsić, J. Plavec, G. Lazarevski,
P. Tepeš, and N. Košutić-Hulita, Bioorg. Med. Chem. 17 (2009)
5857–5867.
15. P. Novak, K. Pičuljan, T. Hrenar, T. Biljan, and Z. Meić, J. Mol.
Struct. 919 (2009) 66–71.
16. P. Novak, K. Pičuljan, T. Hrenar, and V. Smrečki, Croat. Chem.
Acta 82 (2) (2009) 477–483.
Croat. Chem. Acta 85 (2012) 451.
17. P. Novak, K. Pičuljan, T. Biljan, T. Hrenar, M. Cindrić, M.
Rubčić, and Z. Meić, Croat. Chem. Acta 80 (3–4) (2007) 575–581.
18. T. Jednačak, P. Novak, K. Užarević, I. Bratoš, J. Marković, and
M. Cindrić, Croat. Chem. Acta 84 (2011) 203–209.
19. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A.
Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci,
G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P.
Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L.
Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Ha-
segawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai,
T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M.
Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov,
R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C.
Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M.
Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C.
Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev,
A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Mar-
tin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J.
J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B.
Foresman, J. V. Ortiz, J. Cioslowski, and D. J. Fox, Gaussian 09,
Revision A.02, Gaussian, Inc., Wallingford CT, 2009.
20. A. D. Becke, J. Chem. Phys. 98 (1993) 5648–5652.
21. C. Lee, W. Yang, and R. G. Parr, Phys. Rev. B 37 (1988) 785–789.
22. S. Miertuš, E. Scrocco, and J. Tomasi, Chem. Phys. 55 (1981)
117–129.
23. J. Tomasi and M. Persico, Chem. Rev. 94 (1994) 2027–2094.
24. E. Cancès and B. Mennucci, J. Math. Chem. 23 (1998) 309–326.
25. E. Cancès, B. Mennucci, and J. Tomasi, J. Chem. Phys. 107
(1997) 3032–3041.
26. B. Mennucci, E. Cancès, and J. Tomasi, J. Phys. Chem. B 101
(1997) 10506–10517.
27. B. Mennucci, R. Cammi, and J. Tomasi, J. Chem. Phys. 109
(1998) 2798–2807.
28. R. Cammi, B. Mennucci, and J. Tomasi, J. Chem. Phys. 110
(1999) 7627−7638.
29. R. Cammi, J. Chem. Phys. 109 (1998) 3185−3196.
30. Y. H. Lu, Y. W. Lu, C. L. Wu, Q. Shao, X. L. Chen, and R.
Bimbong, Spectrochim. Acta Part A 65 (2006) 695–701.
31. N. Galić, M. Rubčić, K. Magdić, M. Cindrić, and V. Tomišić,
Inorg. Chim. Acta 366 (2011) 98–104.
32. S. Uchiyama, M. Ando, and S. Aoyagi, J. Chromatogr. A 996
(2003) 95–102.
33. N. Galić, A. Dijanošić, D. Kontrec, and S. Miljanić,
Spectrochim. Acta Part A 95 (2012) 347–353.
34. N. Galić, Z. Cimerman, and V. Tomišić, Spectrochim. Acta Part
A 71 (2008) 1274–1280.
35. G. A. Ibáñez, A. C. Olivieri, and G. M. Escandar, J. Chem. Soc.
Farady Trans. 93 (1997) 545–551.
36. G. A. Jeffrey and W. Saenger, Hydrogen Bonding in Biological
Structures, Springer-Verlag, Berlin, 1991.